Synthesis of Acyclic Unsaturated Sugar Derivatives
Starting from the new (2E)-4,5,6,7-tetra-O-acetyl-2,3-dideoxy-aidehydo-D-arabino-hept-2-enose (2), or the previously described (2E)-4, 5, 6-tri-O-acetyl-2,3-dideoxy-aldehydo-D-erythro-hex-2-enose (4), a series of acyclic unsaturated sugar derivatives have been synthetized. Compounds 2 and 4 reacted...
Gespeichert in:
Veröffentlicht in: | Journal of carbohydrate chemistry 1992-01, Vol.11 (1), p.1-19 |
---|---|
Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
Zusammenfassung: | Starting from the new (2E)-4,5,6,7-tetra-O-acetyl-2,3-dideoxy-aidehydo-D-arabino-hept-2-enose (2), or the previously described (2E)-4, 5, 6-tri-O-acetyl-2,3-dideoxy-aldehydo-D-erythro-hex-2-enose (4), a series of acyclic unsaturated sugar derivatives have been synthetized. Compounds 2 and 4 reacted with DBU, leading to 9:1 (2E,4Z)- and (2E,4E)-4-acetoxydienal mixtures. The unsaturated aldimines 10-12 were obtained by reaction of 4 or the dienals 8+9 with primary amines. Selective reduction of aldimines afforded their corresponding allylamines. |
---|---|
ISSN: | 0732-8303 1532-2327 |
DOI: | 10.1080/07328309208016138 |